#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/23/2222367.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222367
loop_
_publ_author_name
'Elizondo, Perla'
'Bernès, Sylvain'
'Nájera, Blanca'
'Góngora, Francisco'
_publ_section_title
;N,N',N''-Tris(2-nitrobenzyl)-2,2',2''-nitrilotriethanaminium
 trichloride 1.41-hydrate
;
_journal_coeditor_code           IM2103
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1616
_journal_page_last               o1617
_journal_paper_doi               10.1107/S1600536809022399
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C27 H36 N7 O6 3+, 3Cl -, 1.41H2 O'
_chemical_formula_moiety         'C27 H36 N7 O6 3+, 3(Cl -), 1.41(H2 O)'
_chemical_formula_sum            'C27 H38.83 Cl3 N7 O7.41'
_chemical_formula_weight         686.47
_chemical_name_systematic
;
N,N',N''-Tris(2-nitrobenzyl)-2,2',2''-
nitrilotriethanaminium trichloride 1.41-hydrate
;
_chemical_temperature_decomposition 504.0(5)
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.190(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.131(2)
_cell_length_b                   13.009(4)
_cell_length_c                   28.071(7)
_cell_measurement_reflns_used    69
_cell_measurement_temperature    298.0(10)
_cell_measurement_theta_max      12.50
_cell_measurement_theta_min      4.63
_cell_volume                     3325.5(15)
_computing_cell_refinement       'XSCANS (Siemens, 1996)'
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'XSCANS (Siemens, 1996)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298.0(10)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       2θ/ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            16115
_diffrn_reflns_theta_full        26.25
_diffrn_reflns_theta_max         26.25
_diffrn_reflns_theta_min         2.14
_diffrn_standards_decay_%        3.5
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_correction_T_min  0.819
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XSCANS; Siemens, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1441
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.340
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     438
_refine_ls_number_reflns         6712
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0557
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0754P)²+1.5076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1458
_refine_ls_wR_factor_ref         0.1754
_reflns_number_gt                4181
_reflns_number_total             6712
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2103.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_temperature_decomposition' since the value had been given
as '503.5--504.5 (dec.)'. The value was changed to '504.0(5)' - the
average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_temperature_decomposition' since the value had been given
as '503.5--504.5 (dec.)'. The value was changed to '504.0(5)' - the
average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3326(2)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2222367
_cod_database_fobs_code          2222367
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.9829(3) 0.79136(19) 0.17125(9) 0.0624(6) Uani d . 1 . .
C C1 0.9926(4) 0.8169(3) 0.22199(11) 0.0701(8) Uani d . 1 . .
H H1A 0.9977 0.8911 0.2253 0.084 Uiso calc R 1 . .
H H1B 1.0831 0.7887 0.2368 0.084 Uiso calc R 1 . .
C C2 0.8671(4) 0.7782(3) 0.24840(11) 0.0690(8) Uani d . 1 . .
H H2A 0.8467 0.7074 0.2393 0.083 Uiso calc R 1 . .
H H2B 0.8945 0.7797 0.2824 0.083 Uiso calc R 1 . .
N N2 0.7313(3) 0.8412(2) 0.23819(8) 0.0586(6) Uani d D 1 . .
H H2C 0.758(3) 0.9045(12) 0.2481(11) 0.070 Uiso d D 1 . .
H H2D 0.706(3) 0.844(2) 0.2064(4) 0.070 Uiso d D 1 . .
C C3 0.6071(4) 0.7981(2) 0.26312(11) 0.0668(8) Uani d . 1 . .
H H3A 0.6416 0.7807 0.2956 0.080 Uiso calc R 1 . .
H H3B 0.5740 0.7352 0.2472 0.080 Uiso calc R 1 . .
C C4 0.4792(3) 0.8706(2) 0.26437(10) 0.0588(7) Uani d . 1 . .
C C5 0.4586(4) 0.9520(2) 0.23318(11) 0.0682(8) Uani d . 1 . .
H H5A 0.5256 0.9624 0.2102 0.082 Uiso calc R 1 . .
C C6 0.3408(4) 1.0185(3) 0.23509(13) 0.0733(9) Uani d . 1 . .
H H6A 0.3284 1.0714 0.2129 0.088 Uiso calc R 1 . .
C C7 0.2432(4) 1.0077(3) 0.26895(13) 0.0736(9) Uani d . 1 . .
H H7A 0.1651 1.0533 0.2702 0.088 Uiso calc R 1 . .
C C8 0.2608(4) 0.9293(3) 0.30119(12) 0.0725(9) Uani d . 1 . .
H H8A 0.1957 0.9216 0.3249 0.087 Uiso calc R 1 . .
C C9 0.3756(4) 0.8620(2) 0.29820(10) 0.0623(8) Uani d . 1 . .
N N3 0.3838(4) 0.7755(3) 0.33158(12) 0.0856(9) Uani d . 1 . .
O O1 0.3524(4) 0.7895(3) 0.37214(12) 0.1437(14) Uani d . 1 . .
O O2 0.4250(4) 0.6941(2) 0.31824(11) 0.1107(10) Uani d . 1 . .
C C11 1.0831(4) 0.8554(3) 0.14559(14) 0.0763(9) Uani d . 1 . .
H H11A 1.0975 0.8234 0.1151 0.092 Uiso calc R 1 . .
H H11B 1.1777 0.8573 0.1637 0.092 Uiso calc R 1 . .
C C12 1.0314(4) 0.9638(3) 0.13682(15) 0.0869(11) Uani d . 1 . .
H H12A 1.0114 0.9950 0.1670 0.104 Uiso calc R 1 . .
H H12B 1.1091 1.0030 0.1235 0.104 Uiso calc R 1 . .
N N12 0.8964(3) 0.9694(2) 0.10352(11) 0.0709(7) Uani d D 1 . .
H H12C 0.907(4) 0.923(2) 0.0803(9) 0.085 Uiso d D 1 . .
H H12D 0.825(3) 0.943(3) 0.1206(11) 0.085 Uiso d D 1 . .
C C13 0.8715(4) 1.0771(3) 0.08618(13) 0.0800(10) Uani d . 1 . .
H H13A 0.9484 1.0955 0.0657 0.096 Uiso calc R 1 . .
H H13B 0.8785 1.1233 0.1134 0.096 Uiso calc R 1 . .
C C14 0.7249(4) 1.0919(2) 0.05908(11) 0.0671(8) Uani d . 1 . .
C C15 0.7256(4) 1.0997(3) 0.01013(12) 0.0784(10) Uani d . 1 . .
H H15A 0.8139 1.0911 -0.0039 0.094 Uiso calc R 1 . .
C C16 0.6024(6) 1.1193(3) -0.01819(15) 0.0926(12) Uani d . 1 . .
H H16A 0.6072 1.1236 -0.0511 0.111 Uiso calc R 1 . .
C C17 0.4729(5) 1.1328(3) 0.00097(16) 0.0919(12) Uani d . 1 . .
H H17A 0.3891 1.1470 -0.0188 0.110 Uiso calc R 1 . .
C C18 0.4635(4) 1.1258(3) 0.04915(17) 0.0858(11) Uani d . 1 . .
H H18A 0.3737 1.1342 0.0623 0.103 Uiso calc R 1 . .
C C19 0.5905(4) 1.1060(2) 0.07840(12) 0.0712(9) Uani d . 1 . .
N N13 0.5780(6) 1.1031(2) 0.12976(14) 0.0969(11) Uani d . 1 . .
O O3 0.4647(6) 1.1270(4) 0.14496(16) 0.1638(18) Uani d . 1 . .
O O4 0.6834(5) 1.0783(2) 0.15623(10) 0.1092(10) Uani d . 1 . .
C C21 1.0212(4) 0.6829(2) 0.16548(11) 0.0679(8) Uani d . 1 . .
H H21A 0.9807 0.6430 0.1906 0.081 Uiso calc R 1 . .
H H21B 1.1272 0.6756 0.1689 0.081 Uiso calc R 1 . .
C C22 0.9657(4) 0.6407(3) 0.11834(13) 0.0758(9) Uani d . 1 . .
H H22A 0.9985 0.6840 0.0931 0.091 Uiso calc R 1 . .
H H22B 1.0057 0.5724 0.1144 0.091 Uiso calc R 1 . .
N N22 0.8036(3) 0.63543(19) 0.11434(9) 0.0648(7) Uani d D 1 . .
H H22C 0.774(4) 0.596(2) 0.1381(9) 0.078 Uiso d D 1 . .
H H22D 0.756(3) 0.6949(15) 0.1190(12) 0.078 Uiso d D 1 . .
C C23 0.7439(4) 0.5962(3) 0.06626(11) 0.0769(10) Uani d . 1 . .
H H23A 0.7383 0.6529 0.0437 0.092 Uiso calc R 1 . .
H H23B 0.8114 0.5457 0.0549 0.092 Uiso calc R 1 . .
C C24 0.5961(5) 0.5488(3) 0.06750(11) 0.0737(9) Uani d . 1 . .
C C25 0.4793(6) 0.6015(4) 0.04688(14) 0.0959(12) Uani d . 1 . .
H H25A 0.4936 0.6668 0.0345 0.115 Uiso calc R 1 . .
C C26 0.3370(7) 0.5587(6) 0.04397(18) 0.1311(19) Uani d . 1 . .
H H26A 0.2571 0.5950 0.0301 0.157 Uiso calc R 1 . .
C C27 0.3195(8) 0.4606(7) 0.0625(2) 0.138(3) Uani d . 1 . .
H H27A 0.2270 0.4303 0.0608 0.166 Uiso calc R 1 . .
C C28 0.4359(10) 0.4094(5) 0.0827(2) 0.140(3) Uani d . 1 . .
H H28A 0.4229 0.3436 0.0946 0.168 Uiso calc R 1 . .
C C29 0.5702(6) 0.4512(3) 0.08602(12) 0.0939(13) Uani d . 1 . .
N N23 0.6930(7) 0.3884(2) 0.10924(12) 0.1083(15) Uani d . 1 . .
O O5 0.6572(7) 0.3081(3) 0.12602(13) 0.205(3) Uani d . 1 . .
O O6 0.8142(6) 0.4235(3) 0.11446(16) 0.1383(14) Uani d . 1 . .
Cl Cl1 0.61515(8) 0.83642(6) 0.12955(2) 0.0618(2) Uani d . 1 . .
Cl Cl2 0.66871(10) 0.53719(6) 0.20643(3) 0.0696(2) Uani d . 1 . .
Cl Cl3 0.91772(12) 0.82403(9) 0.01891(4) 0.0971(3) Uani d . 1 . .
O O7 1.0384(7) 0.6272(5) -0.0268(2) 0.166(3) Uani d PD 0.793(11) . .
H H71 1.046(14) 0.658(7) -0.0533(19) 0.249 Uiso d PD 0.793(11) . .
H H72 1.006(12) 0.673(5) -0.009(3) 0.249 Uiso d PD 0.793(11) . .
O O8 0.3919(5) 0.6773(5) 0.1646(2) 0.121(3) Uani d PD 0.621(9) . .
H H81 0.426(9) 0.723(5) 0.147(3) 0.182 Uiso d PD 0.621(9) . .
H H82 0.461(7) 0.633(6) 0.168(4) 0.182 Uiso d PD 0.621(9) . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-2 0 4
-1 -3 0
1 -3 0
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C11 . . 110.8(3) ?
C1 N1 C21 . . 109.2(2) ?
C11 N1 C21 . . 109.3(3) ?
N1 C1 C2 . . 114.4(3) ?
N1 C1 H1A . . 108.7 ?
C2 C1 H1A . . 108.7 ?
N1 C1 H1B . . 108.7 ?
C2 C1 H1B . . 108.7 ?
H1A C1 H1B . . 107.6 ?
N2 C2 C1 . . 112.0(3) ?
N2 C2 H2A . . 109.2 ?
C1 C2 H2A . . 109.2 ?
N2 C2 H2B . . 109.2 ?
C1 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
C3 N2 C2 . . 110.7(2) ?
C3 N2 H2C . . 114(2) ?
C2 N2 H2C . . 104(2) ?
C3 N2 H2D . . 109(2) ?
C2 N2 H2D . . 111(2) ?
H2C N2 H2D . . 109(3) ?
N2 C3 C4 . . 113.3(3) ?
N2 C3 H3A . . 108.9 ?
C4 C3 H3A . . 108.9 ?
N2 C3 H3B . . 108.9 ?
C4 C3 H3B . . 108.9 ?
H3A C3 H3B . . 107.7 ?
C5 C4 C9 . . 115.3(3) ?
C5 C4 C3 . . 122.5(3) ?
C9 C4 C3 . . 122.2(3) ?
C4 C5 C6 . . 121.7(3) ?
C4 C5 H5A . . 119.1 ?
C6 C5 H5A . . 119.1 ?
C7 C6 C5 . . 120.9(3) ?
C7 C6 H6A . . 119.5 ?
C5 C6 H6A . . 119.5 ?
C6 C7 C8 . . 119.4(3) ?
C6 C7 H7A . . 120.3 ?
C8 C7 H7A . . 120.3 ?
C7 C8 C9 . . 119.3(3) ?
C7 C8 H8A . . 120.4 ?
C9 C8 H8A . . 120.4 ?
C8 C9 C4 . . 123.4(3) ?
C8 C9 N3 . . 117.1(3) ?
C4 C9 N3 . . 119.5(3) ?
O2 N3 O1 . . 122.1(4) ?
O2 N3 C9 . . 119.0(3) ?
O1 N3 C9 . . 118.9(4) ?
N1 C11 C12 . . 114.5(3) ?
N1 C11 H11A . . 108.6 ?
C12 C11 H11A . . 108.6 ?
N1 C11 H11B . . 108.6 ?
C12 C11 H11B . . 108.6 ?
H11A C11 H11B . . 107.6 ?
N12 C12 C11 . . 112.6(3) ?
N12 C12 H12A . . 109.1 ?
C11 C12 H12A . . 109.1 ?
N12 C12 H12B . . 109.1 ?
C11 C12 H12B . . 109.1 ?
H12A C12 H12B . . 107.8 ?
C12 N12 C13 . . 110.5(2) ?
C12 N12 H12C . . 107(2) ?
C13 N12 H12C . . 114(2) ?
C12 N12 H12D . . 104(2) ?
C13 N12 H12D . . 115(2) ?
H12C N12 H12D . . 104(3) ?
N12 C13 C14 . . 113.2(3) ?
N12 C13 H13A . . 108.9 ?
C14 C13 H13A . . 108.9 ?
N12 C13 H13B . . 108.9 ?
C14 C13 H13B . . 108.9 ?
H13A C13 H13B . . 107.8 ?
C15 C14 C19 . . 116.6(3) ?
C15 C14 C13 . . 116.4(3) ?
C19 C14 C13 . . 126.8(3) ?
C16 C15 C14 . . 122.3(4) ?
C16 C15 H15A . . 118.8 ?
C14 C15 H15A . . 118.8 ?
C17 C16 C15 . . 120.5(4) ?
C17 C16 H16A . . 119.8 ?
C15 C16 H16A . . 119.8 ?
C16 C17 C18 . . 120.5(4) ?
C16 C17 H17A . . 119.7 ?
C18 C17 H17A . . 119.7 ?
C17 C18 C19 . . 119.1(4) ?
C17 C18 H18A . . 120.5 ?
C19 C18 H18A . . 120.5 ?
C14 C19 C18 . . 121.0(3) ?
C14 C19 N13 . . 121.3(4) ?
C18 C19 N13 . . 117.8(4) ?
O3 N13 O4 . . 121.4(4) ?
O3 N13 C19 . . 118.8(5) ?
O4 N13 C19 . . 119.8(4) ?
N1 C21 C22 . . 112.6(3) ?
N1 C21 H21A . . 109.1 ?
C22 C21 H21A . . 109.1 ?
N1 C21 H21B . . 109.1 ?
C22 C21 H21B . . 109.1 ?
H21A C21 H21B . . 107.8 ?
N22 C22 C21 . . 111.1(3) ?
N22 C22 H22A . . 109.4 ?
C21 C22 H22A . . 109.4 ?
N22 C22 H22B . . 109.4 ?
C21 C22 H22B . . 109.4 ?
H22A C22 H22B . . 108.0 ?
C22 N22 C23 . . 112.2(3) ?
C22 N22 H22C . . 109(2) ?
C23 N22 H22C . . 111(2) ?
C22 N22 H22D . . 116(2) ?
C23 N22 H22D . . 106(2) ?
H22C N22 H22D . . 102(3) ?
C24 C23 N22 . . 112.9(3) ?
C24 C23 H23A . . 109.0 ?
N22 C23 H23A . . 109.0 ?
C24 C23 H23B . . 109.0 ?
N22 C23 H23B . . 109.0 ?
H23A C23 H23B . . 107.8 ?
C25 C24 C29 . . 117.9(4) ?
C25 C24 C23 . . 117.7(3) ?
C29 C24 C23 . . 124.4(4) ?
C24 C25 C26 . . 121.0(5) ?
C24 C25 H25A . . 119.5 ?
C26 C25 H25A . . 119.5 ?
C27 C26 C25 . . 118.1(6) ?
C27 C26 H26A . . 121.0 ?
C25 C26 H26A . . 121.0 ?
C28 C27 C26 . . 120.2(6) ?
C28 C27 H27A . . 119.9 ?
C26 C27 H27A . . 119.9 ?
C29 C28 C27 . . 121.3(6) ?
C29 C28 H28A . . 119.4 ?
C27 C28 H28A . . 119.4 ?
C28 C29 C24 . . 121.5(6) ?
C28 C29 N23 . . 117.5(5) ?
C24 C29 N23 . . 121.0(4) ?
O6 N23 O5 . . 124.0(6) ?
O6 N23 C29 . . 120.1(4) ?
O5 N23 C29 . . 115.4(6) ?
H71 O7 H72 . . 104(3) ?
H81 O8 H82 . . 104(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . 1.459(4) ?
N1 C11 . 1.465(4) ?
N1 C21 . 1.466(4) ?
C1 C2 . 1.497(5) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 N2 . 1.497(4) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
N2 C3 . 1.485(4) ?
N2 H2C . 0.897(10) ?
N2 H2D . 0.906(10) ?
C3 C4 . 1.504(4) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.378(4) ?
C4 C9 . 1.393(4) ?
C5 C6 . 1.385(5) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.357(5) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.365(5) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.372(5) ?
C8 H8A . 0.9300 ?
C9 N3 . 1.463(4) ?
N3 O2 . 1.193(4) ?
N3 O1 . 1.208(4) ?
C11 C12 . 1.501(5) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 N12 . 1.493(4) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
N12 C13 . 1.495(4) ?
N12 H12C . 0.897(10) ?
N12 H12D . 0.902(10) ?
C13 C14 . 1.503(5) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.378(5) ?
C14 C19 . 1.389(5) ?
C15 C16 . 1.354(5) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.346(6) ?
C16 H16A . 0.9300 ?
C17 C18 . 1.364(6) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.396(5) ?
C18 H18A . 0.9300 ?
C19 N13 . 1.455(5) ?
N13 O3 . 1.190(5) ?
N13 O4 . 1.216(5) ?
C21 C22 . 1.487(5) ?
C21 H21A . 0.9700 ?
C21 H21B . 0.9700 ?
C22 N22 . 1.478(5) ?
C22 H22A . 0.9700 ?
C22 H22B . 0.9700 ?
N22 C23 . 1.507(4) ?
N22 H22C . 0.899(10) ?
N22 H22D . 0.900(10) ?
C23 C24 . 1.487(5) ?
C23 H23A . 0.9700 ?
C23 H23B . 0.9700 ?
C24 C25 . 1.361(6) ?
C24 C29 . 1.398(5) ?
C25 C26 . 1.411(7) ?
C25 H25A . 0.9300 ?
C26 C27 . 1.391(9) ?
C26 H26A . 0.9300 ?
C27 C28 . 1.345(9) ?
C27 H27A . 0.9300 ?
C28 C29 . 1.338(8) ?
C28 H28A . 0.9300 ?
C29 N23 . 1.498(7) ?
N23 O6 . 1.196(6) ?
N23 O5 . 1.202(5) ?
O7 H71 . 0.851(10) ?
O7 H72 . 0.851(10) ?
O8 H81 . 0.850(10) ?
O8 H82 . 0.850(10) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2D Cl1 . 0.906(10) 2.255(11) 3.155(2) 172(3) yes
N12 H12D Cl1 . 0.902(10) 2.396(19) 3.225(3) 153(3) yes
N22 H22D Cl1 . 0.900(10) 2.279(11) 3.176(3) 174(3) yes
N12 H12C Cl3 . 0.897(10) 2.161(11) 3.054(3) 174(3) yes
N22 H22C Cl2 . 0.899(10) 2.335(14) 3.209(3) 164(3) yes
O8 H81 Cl1 . 0.850(10) 2.35(5) 3.115(5) 150(9) yes
O8 H82 Cl2 . 0.850(10) 2.46(4) 3.265(5) 159(10) yes
O7 H72 Cl3 . 0.851(10) 2.28(3) 3.102(6) 163(9) yes
N2 H2C Cl2 2_655 0.897(10) 2.221(14) 3.089(3) 163(3) yes
O7 H71 O6 3_765 0.851(10) 2.45(8) 2.965(7) 119(8) yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 N1 C1 C2 . . . . 163.5(3) ?
C21 N1 C1 C2 . . . . -76.1(3) ?
N1 C1 C2 N2 . . . . -75.8(3) ?
C1 C2 N2 C3 . . . . 177.4(2) ?
C2 N2 C3 C4 . . . . 165.9(2) ?
N2 C3 C4 C5 . . . . 19.9(4) ?
N2 C3 C4 C9 . . . . -158.0(3) ?
C9 C4 C5 C6 . . . . -1.4(4) ?
C3 C4 C5 C6 . . . . -179.5(3) ?
C4 C5 C6 C7 . . . . 2.0(5) ?
C5 C6 C7 C8 . . . . -0.8(5) ?
C6 C7 C8 C9 . . . . -1.0(5) ?
C7 C8 C9 C4 . . . . 1.7(5) ?
C7 C8 C9 N3 . . . . -176.1(3) ?
C5 C4 C9 C8 . . . . -0.5(4) ?
C3 C4 C9 C8 . . . . 177.6(3) ?
C5 C4 C9 N3 . . . . 177.2(3) ?
C3 C4 C9 N3 . . . . -4.7(4) ?
C8 C9 N3 O2 . . . . 143.3(4) ?
C4 C9 N3 O2 . . . . -34.6(5) ?
C8 C9 N3 O1 . . . . -38.7(5) ?
C4 C9 N3 O1 . . . . 143.5(4) ?
C1 N1 C11 C12 . . . . -76.1(3) ?
C21 N1 C11 C12 . . . . 163.6(3) ?
N1 C11 C12 N12 . . . . -66.1(4) ?
C11 C12 N12 C13 . . . . -165.5(3) ?
C12 N12 C13 C14 . . . . -170.5(3) ?
N12 C13 C14 C15 . . . . -104.5(4) ?
N12 C13 C14 C19 . . . . 80.5(4) ?
C19 C14 C15 C16 . . . . -0.4(5) ?
C13 C14 C15 C16 . . . . -175.9(3) ?
C14 C15 C16 C17 . . . . 0.4(6) ?
C15 C16 C17 C18 . . . . -0.6(6) ?
C16 C17 C18 C19 . . . . 0.9(6) ?
C15 C14 C19 C18 . . . . 0.7(5) ?
C13 C14 C19 C18 . . . . 175.6(3) ?
C15 C14 C19 N13 . . . . -177.8(3) ?
C13 C14 C19 N13 . . . . -2.9(5) ?
C17 C18 C19 C14 . . . . -1.0(5) ?
C17 C18 C19 N13 . . . . 177.6(3) ?
C14 C19 N13 O3 . . . . 171.6(4) ?
C18 C19 N13 O3 . . . . -6.9(5) ?
C14 C19 N13 O4 . . . . -7.1(5) ?
C18 C19 N13 O4 . . . . 174.3(3) ?
C1 N1 C21 C22 . . . . 159.9(3) ?
C11 N1 C21 C22 . . . . -78.8(3) ?
N1 C21 C22 N22 . . . . -67.4(4) ?
C21 C22 N22 C23 . . . . 178.1(3) ?
C22 N22 C23 C24 . . . . 155.5(3) ?
N22 C23 C24 C25 . . . . 107.9(4) ?
N22 C23 C24 C29 . . . . -75.9(4) ?
C29 C24 C25 C26 . . . . -0.5(5) ?
C23 C24 C25 C26 . . . . 176.0(3) ?
C24 C25 C26 C27 . . . . -0.5(6) ?
C25 C26 C27 C28 . . . . 0.4(8) ?
C26 C27 C28 C29 . . . . 0.6(8) ?
C27 C28 C29 C24 . . . . -1.7(7) ?
C27 C28 C29 N23 . . . . 179.9(5) ?
C25 C24 C29 C28 . . . . 1.6(5) ?
C23 C24 C29 C28 . . . . -174.6(4) ?
C25 C24 C29 N23 . . . . 180.0(3) ?
C23 C24 C29 N23 . . . . 3.8(5) ?
C28 C29 N23 O6 . . . . -177.6(4) ?
C24 C29 N23 O6 . . . . 3.9(6) ?
C28 C29 N23 O5 . . . . -5.1(5) ?
C24 C29 N23 O5 . . . . 176.4(4) ?
